EP0339712A1 - Method for preparing flat or semi-flat water paints - Google Patents
Method for preparing flat or semi-flat water paints Download PDFInfo
- Publication number
- EP0339712A1 EP0339712A1 EP89200938A EP89200938A EP0339712A1 EP 0339712 A1 EP0339712 A1 EP 0339712A1 EP 89200938 A EP89200938 A EP 89200938A EP 89200938 A EP89200938 A EP 89200938A EP 0339712 A1 EP0339712 A1 EP 0339712A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polyurethane
- flat
- cellulose ether
- viscosity
- semi
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/43—Thickening agents
- C09D7/44—Combinations of two or more thickening agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
- C08L1/26—Cellulose ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
Definitions
- the present invention relates to a method for preparing flat and/or semi-flat water paints, a water-soluble nonionic cellulose ether and an associative polyurethane being added as rheology- and performance-improving agents.
- cellulose ethers are advantageous in that they produce the desired effect at a low cost and yield a good texture (grain).
- the viscosity-increasing effect is relatively unaffected by additives, such as tinting colorants.
- additives such as tinting colorants.
- cellulose ethers give relatively low viscosities at high shear rates, and poor levelling, which means inadequate hiding power.
- flat and semi-flat water paints with excellent properties can be obtained at low costs by combining a nonionic water-soluble cellulose ether with an associative polyurethane thickener, the weight ratio of polyurethane thickener and cellulose ether being 2:8-8:2.
- "flat and semi-flat" paints relates to paints having a pigment volume concentration of at least 30%.
- "associative polyurethane thickener” relates to a polymer containing at least 2, suitably 3 or more hydrophobic groups having 6-30 carbon atoms with intermediate hydrophilic polyether segments, the hydrophobic groups and the hydrophilic segments being interlinked to an essential extent by urethane bonds. They usually have a molecular weight of 10,000-250,000, preferably 15,000-100,000. A large number of such compounds are known and described, e.g. in US Patent Specifications 2,946,767 and 4,079,028 and European Patent Publication 96,882, of which relevant portions are included by reference in the present specification.
- the water-soluble nonionic cellulose ether may have both alkyl substituents and hydroxyalkyl substituents or combinations thereof.
- suitable nonionic cellulose derivatives are methylcellulose, methylhydroxyethylcellulose, methylhydroxypropylcellulose, hydroxyethylcellulose, hydroxyethylhydroxypropylcellulose, hydroxyethylhydroxybutylcellulose, ethylhydroxyethylcellulose and propylhydroxyethylcellulose.
- the above-mentioned cellulose ethers may also contain a minor amount of hydrocarbon substituents having 4-20 carbon atoms, such as benzyl, dodecyl, octyl and decyl substituents, provided the cellulose ethers become water-soluble.
- Preferred cellulose ethers are such ethers as contain an alkyl group, such as a methyl or an ethyl group.
- the nonionic cellulose ethers preferably have a viscosity of 5,000-150,000 mPa ⁇ s in a 2% aqueous solution measured on a Brookfield viscometer. A suitable flocculation temperature is 50-80°C.
- Suitable binders are alkyd resins and latex binders, such as polyvinylacetate, polyacrylate, copolymers of vinylacetate and acrylate, copolymers of vinylacetate and ethylene, copolymers of vinylacetate, ethylene and vinylchloride and copolymers of styrene and acrylate.
- the present invention is further illustrated by the following Example.
- a levelling value of 3-6 gives a suitable texture for a flat or semi-flat paint.
- a levelling value of 9 or 10 indicates excellent levelling which is however not desirable for flat or semi-flat paints because of the resulting unsatisfactory texture. From the results appears that additives 2-15 according to the invention, all of which have the same viscosity at low shear rates, have a levelling value essentially better adapted to flat and semi-flat paints than when polyurethane alone is used as thickener.
- Example 2 The same paints as in Example 1 were admixed with additives 1, 4, 7, 9, 11, 13 or 15 according to Example 1 and 5% by weight, based on the weight of the paint, of any of the tinting colorants Colortrend Thalo Blue and Colortrend Lamp Black. The viscosity was thereafter determined at low shear rates. The following results were obtained. Table 3 Additive Viscosity, KU Acrylic binder Vinyl-acrylic binder Thalo Blue Lamp Black Thalo Blue Lamp Black 1 86 97 112 138 4 92 100 114 120 7 108 108 - - 9 109 109 - - 11 101 109 - - 13 - 123 125 15 - - 120 125
- Example 2 The same flat paints as in Example 1 were admixed with one of the additives stated below in such amounts that they had the same viscosity at low shear rates.
- the components are the same as in Example 1.
- Table 4 Additive Added amount, % by weight of paint Acrylic binder Vinyl-acrylic binder 1.
- Ethylhydroxyethylcellulose B 0.86 0.80 2.
- Ethylhydroxyethylcellulose B 0.41 0.50 Polyurethane A 0.40 0.40 5.
- Ethylhydroxyethylcellulose C 0.49 0.50 Polyurethane A 0.20 0.20 6.
- compositions obtained all of which had a viscosity of 122 KU at low shear rates, were then tested for viscosity at high shear rates using an ICI viscometer. The following results were obtained.
- Table 5 Additive Viscosity, ICI, Poise Acrylic binder Vinyl-acrylic binder 1 1.4 1.8 2 1.2 1.6 3 1.6 1.8 4 1.8 2.0 5 1.4 1.7 6 1.6 1.8 7 2.0 - 8 2.0 - 9 1.6 - 10 2.1 - 11 1.8 - 12 2.1 - 13 - 1.9 14 - 2.0 15 - 1.6 16 - 1.8
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
Abstract
Description
- The present invention relates to a method for preparing flat and/or semi-flat water paints, a water-soluble nonionic cellulose ether and an associative polyurethane being added as rheology- and performance-improving agents.
- In the making of flat or semi-flat water paints, it is customary to use cellulose ethers as thickeners. Cellulose ethers are advantageous in that they produce the desired effect at a low cost and yield a good texture (grain). The viscosity-increasing effect is relatively unaffected by additives, such as tinting colorants. On the other hand, with increasing molecular weights cellulose ethers give relatively low viscosities at high shear rates, and poor levelling, which means inadequate hiding power.
- It has therefore been suggested to replace the cellulose ethers with an associative thickener of the polyurethane type. It is true that the associative polyurethanes give improved viscosity at high shear rates, but they also give a poor texture (grain), which is linked with extreme levelling. The associative polyurethanes therefore have not been commonly used as rheology- and performance-improving agents for flat or semi-flat paints.
- It has now been found that flat and semi-flat water paints with excellent properties can be obtained at low costs by combining a nonionic water-soluble cellulose ether with an associative polyurethane thickener, the weight ratio of polyurethane thickener and cellulose ether being 2:8-8:2. In the present context, "flat and semi-flat" paints relates to paints having a pigment volume concentration of at least 30%. By combining a nonionic water-soluble cellulose ether with an associa tive polyurethane thickener, it has proved possible to essentially maintain the positive characteristics of the two components while suppressing their negative characteristics.
- In the present context, "associative polyurethane thickener" relates to a polymer containing at least 2, suitably 3 or more hydrophobic groups having 6-30 carbon atoms with intermediate hydrophilic polyether segments, the hydrophobic groups and the hydrophilic segments being interlinked to an essential extent by urethane bonds. They usually have a molecular weight of 10,000-250,000, preferably 15,000-100,000. A large number of such compounds are known and described, e.g. in US Patent Specifications 2,946,767 and 4,079,028 and European Patent Publication 96,882, of which relevant portions are included by reference in the present specification.
- The water-soluble nonionic cellulose ether may have both alkyl substituents and hydroxyalkyl substituents or combinations thereof. Typical examples of suitable nonionic cellulose derivatives are methylcellulose, methylhydroxyethylcellulose, methylhydroxypropylcellulose, hydroxyethylcellulose, hydroxyethylhydroxypropylcellulose, hydroxyethylhydroxybutylcellulose, ethylhydroxyethylcellulose and propylhydroxyethylcellulose. The above-mentioned cellulose ethers may also contain a minor amount of hydrocarbon substituents having 4-20 carbon atoms, such as benzyl, dodecyl, octyl and decyl substituents, provided the cellulose ethers become water-soluble. Preferred cellulose ethers are such ethers as contain an alkyl group, such as a methyl or an ethyl group. The nonionic cellulose ethers preferably have a viscosity of 5,000-150,000 mPa·s in a 2% aqueous solution measured on a Brookfield viscometer. A suitable flocculation temperature is 50-80°C.
- The positive effects of the invention have been observed on paints based on a number of binders which differ essentially from each other. Suitable binders are alkyd resins and latex binders, such as polyvinylacetate, polyacrylate, copolymers of vinylacetate and acrylate, copolymers of vinylacetate and ethylene, copolymers of vinylacetate, ethylene and vinylchloride and copolymers of styrene and acrylate.
- The present invention is further illustrated by the following Example.
- A flat indoor paint having a pigment volume concentration of 46% and a dry solids content of 54% by weight and containing 25% by weight of a polyacrylate binder, Rhoplex AC-64, alternatively a binder consisting of a copolymer of vinylacetate and acrylate, UCAR 367, was admixed with one of the additives stated below in such amounts that the paints had a viscosity of 122 KU at low shear rates measured according to ASTM C 562-81. The following results were obtained. The indicated amounts relate to active content.
Table 1 Additive Amount, % by weight of paint Acrylic binder Vinyl-acrylic binder 1. Polyurethane A1/ 0.67 0.72 2. Ethylhydroxyethylcellulose B2/ 0.63 0.64 Polyurethane A 0.20 0.20 3. Ethylhydroxyethylcellulose C3/ 0.49 0.50 Polyurethane A 0.20 0.20 4. Ethylhydroxyethylcellulose B 0.41 0.50 Polyurethane A 0.40 0.40 5. Ethylhydroxyethylcellulose C 0.32 0.38 Polyurethane A 0.40 0.40 6. Hydroxypropylmethylcellulose F4/ 0.70 - Polyurethane A 0.20 - 7. Hydroxypropylmethylcellulose F 0.50 - Polyurethane A 0.40 - 8. Ethylhydroxyethylcellulose B 0.50 - Polyurethane D5/ 0.20 - 9. Ethylhydroxyethylcellulose B 0.35 - Polyurethane D 0.40 - 10. Ethylhydroxyethylcellulose B 0.55 - Polyurethane E6/ 0.20 - 11. Ethylhydroxyethylcellulose B 0.40 - Polyurethane E 0.40 - 12. Hydroxyethylcellulose G7/ - 0.64 Polyurethane A - 0.20 13. Hydroxyethylcellulose G - 0.50 Polyurethane A 0.40 14. Hydroxyethylcellulose H8/ - 0.50 Polyurethane A - 0.20 15. Hydroxyethylcellulose H - 0.38 Polyurethane A - 0.40 -
- 1) Polyurethane A (BERMODOL PUR 2100) is an associative polyurethane thickener containing two major hydrophobic hydrocarbon groups and hydrophilic polyether chains. Viscosity is 1500 mPa·s (Brookfield) at 12 rpm and dry solids content 35% by weight.
- 2) Ethylhydroxyethylcellulose B (BERMOCOLL E 411 FQ) has a flocculation temperature of about 70°C and a viscosity in 2% solution of 12,000 mPa·s (Brookfield) at 12 rpm.
- 3) Ethylhydroxyethylcellulose C (BERMOCOLL E 481 FQ) has a flocculation temperature of about 70°C and a viscosity in 2% solution of 80,000 mPa·s (Brookfield) at 6 rpm.
- 4) Hydroxypropylmethylcellulose F (Methocel J5MS) has a gelling temperature of 56°C and a viscosity of 5,000 mPa·s (Ubbelohde) in 2% solution.
- 5) Polyurethane D (Acrysol RM-825) is an associative polyurethane thickener and has a viscosity of 1,000-2,500 mPa·s (Brookfield) and a dry solids content of 25% by weight.
- 6) Polyurethane E (UCAR SCT-270) is an associative polyurethane thickener and has a viscosity of 6,000-10,000 mPa·s (Brookfield) and a dry solids content of 20% by weight.
- 7) Hydroxyethylcellulose G (Cellosize QP 4400) has a flocculation temperature of >100°C and a viscosity in 2% solution of 4,800-6,000 mPa·s at 60 rpm (Brookfield).
- 8) Hydroxyethylcellulose H (Natrosol 250 HHR) has a flocculation temperature of >100°C and a viscosity in 2% solution of about 100,000 mPa·s at 6 rpm (Brookfield).
- The different paints were then tested for levelling according to ASTM D4062-81, the following results being obtained.
Table 2 Additive Levelling Acrylic binder Vinyl-acrylic binder 1 10 9 2 5 2 3 3 2 4 8 3 5 7 4 6 2 - 7 5 - 8 3 - 9 6 - 10 3 - 11 5 - 12 - 2 13 - 3 14 - 2 15 - 3 - A levelling value of 3-6 gives a suitable texture for a flat or semi-flat paint. A levelling value of 9 or 10 indicates excellent levelling which is however not desirable for flat or semi-flat paints because of the resulting unsatisfactory texture. From the results appears that additives 2-15 according to the invention, all of which have the same viscosity at low shear rates, have a levelling value essentially better adapted to flat and semi-flat paints than when polyurethane alone is used as thickener.
- The same paints as in Example 1 were admixed with additives 1, 4, 7, 9, 11, 13 or 15 according to Example 1 and 5% by weight, based on the weight of the paint, of any of the tinting colorants Colortrend Thalo Blue and Colortrend Lamp Black. The viscosity was thereafter determined at low shear rates. The following results were obtained.
Table 3 Additive Viscosity, KU Acrylic binder Vinyl-acrylic binder Thalo Blue Lamp Black Thalo Blue Lamp Black 1 86 97 112 138 4 92 100 114 120 7 108 108 - - 9 109 109 - - 11 101 109 - - 13 - - 123 125 15 - - 120 125 - The viscosities obtained should be compared with 122 KU, which was the viscosity of the paints without the addition of a tinting colorant. From the results appears that the changes in viscosity are considerably less for additives 4, 7, 9, 11, 13 and 15 according to the invention than for reference additive 1.
- The same flat paints as in Example 1 were admixed with one of the additives stated below in such amounts that they had the same viscosity at low shear rates. The components are the same as in Example 1.
Table 4 Additive Added amount, % by weight of paint Acrylic binder Vinyl-acrylic binder 1. Ethylhydroxyethylcellulose B 0.86 0.80 2. Ethylhydroxyethylcellulose C 0.67 0.58 3. Ethylhydroxyethylcellulose B 0.63 0.64 Polyurethane A 0.20 0.20 4. Ethylhydroxyethylcellulose B 0.41 0.50 Polyurethane A 0.40 0.40 5. Ethylhydroxyethylcellulose C 0.49 0.50 Polyurethane A 0.20 0.20 6. Ethylhydroxyethylcellulose C 0.32 0.38 Polyurethane A 0.40 0.40 7. Hydroxypropylmethylcellulose F 0.70 - Polyurethane A 0.20 - 8. Hydroxypropylmethylcellulose F 0.50 - Polyurethane A 0.40 - 9. Ethylhydroxyethylcellulose B 0.50 - Polyurethane D 0.20 - 10. Ethylhydroxyethylcellulose B 0.35 - Polyurethane D 0.40 - 11. Ethylhydroxyethylcellulose B 0.55 - Polyurethane E 0.20 - 12. Ethylhydroxyethylcellulose B 0.40 - Polyurethane E 0.40 - 13. Hydroxyethylcellulose G - 0.64 Polyurethane A - 0.20 14. Hydroxyethylcellulose G - 0.50 Polyurethane A 0.40 15. Hydroxyethylcellulose H - 0.50 Polyurethane A - 0.20 16. Hydroxyethylcellulose H - 0.38 Polyurethane A - 0.40 - The compositions obtained, all of which had a viscosity of 122 KU at low shear rates, were then tested for viscosity at high shear rates using an ICI viscometer. The following results were obtained.
Table 5 Additive Viscosity, ICI, Poise Acrylic binder Vinyl-acrylic binder 1 1.4 1.8 2 1.2 1.6 3 1.6 1.8 4 1.8 2.0 5 1.4 1.7 6 1.6 1.8 7 2.0 - 8 2.0 - 9 1.6 - 10 2.1 - 11 1.8 - 12 2.1 - 13 - 1.9 14 - 2.0 15 - 1.6 16 - 1.8 - From the results appears that in those cases where the cellulose ethers gave a viscosity which was relatively low at high shear rates, it was possible to notably improve the viscosity by adding an associative polyurethane thickener without any change of the viscosity at low shear rates.
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT89200938T ATE80407T1 (en) | 1988-04-28 | 1989-04-14 | METHOD OF MAKING MATTE OR SEMI-MATT WATERCOLORS. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE8801594 | 1988-04-28 | ||
SE8801594A SE459096B (en) | 1988-04-28 | 1988-04-28 | SET TO MAKE MATT OR HALF-MATT WATER-BORN MAALARFERGER |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0339712A1 true EP0339712A1 (en) | 1989-11-02 |
EP0339712B1 EP0339712B1 (en) | 1992-09-09 |
Family
ID=20372158
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP89200938A Expired - Lifetime EP0339712B1 (en) | 1988-04-28 | 1989-04-14 | Method for preparing flat or semi-flat water paints |
Country Status (5)
Country | Link |
---|---|
US (1) | US5002985A (en) |
EP (1) | EP0339712B1 (en) |
AT (1) | ATE80407T1 (en) |
DE (1) | DE68902766T2 (en) |
SE (1) | SE459096B (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0566911A1 (en) * | 1992-04-20 | 1993-10-27 | Aqualon Company | Improved leveling aqueous coating compositions |
WO1997025382A1 (en) * | 1996-01-09 | 1997-07-17 | Henkel Kommanditgesellschaft Auf Aktien | Liquid preparation of thickening agents (ii) |
WO1999040893A1 (en) * | 1998-02-13 | 1999-08-19 | L'oreal | Cosmetic composition based on associative polyurethane and non-ionic polymers with fatty chains |
EP0979850A1 (en) * | 1998-08-11 | 2000-02-16 | Hercules Incorporated | Use of aqueous protective coating compositions for industrial coatings and aqueous coating compositions |
US6258367B1 (en) | 1998-02-13 | 2001-07-10 | L'oreal | Cosmetic composition comprising at least one nonionic amphiphilic associative polyurethane and at least one quaternary silicone |
US6572869B2 (en) | 1998-02-13 | 2003-06-03 | L'oreal S.A. | Cosmetic compositions comprising at least one catonic polymer and at least one nonionic associative polymer |
EP1464686A1 (en) * | 2003-04-02 | 2004-10-06 | Reinol S.p.A. | Pseudoplastic water based ink for ball-point pen |
WO2008125977A2 (en) * | 2007-04-17 | 2008-10-23 | Akzo Nobel Coatings International B.V. | A painting apparatus |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0384167B1 (en) | 1989-01-31 | 1994-07-06 | Union Carbide Chemicals And Plastics Company, Inc. | Polysaccharides with alkaryl or aralkyl hydrophobes and latex compositions containing same |
EP0642557B1 (en) * | 1992-05-29 | 1999-02-24 | Henkel Corporation | Method of modifying the rheological properties of latex paint |
US5281654A (en) * | 1993-01-14 | 1994-01-25 | Rohm And Haas Company | Polyurethane mixture |
US5504123A (en) * | 1994-12-20 | 1996-04-02 | Union Carbide Chemicals & Plastics Technology Corporation | Dual functional cellulosic additives for latex compositions |
FR2733910B1 (en) | 1995-05-12 | 1997-06-27 | Oreal | COMPOSITION IN THE FORM OF AEROSOL FOAM BASED ON POLYURETHANE AND ANIONIC POLYMER |
DE69925707T2 (en) * | 1999-03-05 | 2006-03-23 | Hercules Inc., Wilmington | Cellulosic associative thickeners having a high ICI viscosity |
US20030012946A1 (en) * | 2001-06-28 | 2003-01-16 | Davis Stephen C. | Coated polymeric foam |
US7121036B1 (en) * | 2004-12-23 | 2006-10-17 | Raytheon Company | Method and apparatus for safe operation of an electronic firearm sight depending upon the detection of a selected color |
BRPI0615727A2 (en) * | 2005-09-07 | 2016-08-23 | Elementis Specialties Inc | waterborne latex ink system, method for formulating a waterborne latex ink system, and polymeric chemical |
WO2007056070A2 (en) * | 2005-11-04 | 2007-05-18 | Hercules Incorporated | Ether derivatives of raw cotton linters for water-borne coatings |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1669114A1 (en) * | 1965-09-02 | 1971-12-23 | Dow Chemical Co | Thickener for aqueous latex coatings |
EP0127950A1 (en) * | 1983-05-03 | 1984-12-12 | Rheox International, Inc. | Preparation of water dispersible, modified polyurethanes |
EP0250943A2 (en) * | 1986-06-12 | 1988-01-07 | DeSoto, Inc. | Nonionic associative thickeners |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2210483B2 (en) * | 1972-03-04 | 1980-01-03 | Basf Ag, 6700 Ludwigshafen | Coating, impregnation and bonding agents |
US4137209A (en) * | 1977-11-14 | 1979-01-30 | Owens-Corning Fiberglas Corporation | Glass fiber size composition |
JPS572367A (en) * | 1980-06-07 | 1982-01-07 | Kansai Paint Co Ltd | Water-dispersed thermosetting resin slurry paint composition |
DE3633365A1 (en) * | 1986-10-01 | 1988-04-14 | Bayer Ag | If appropriate, cell-shaped polyurethanes, which have been connected or made up with another material, and process for their production |
-
1988
- 1988-04-28 SE SE8801594A patent/SE459096B/en not_active IP Right Cessation
-
1989
- 1989-04-13 US US07/337,751 patent/US5002985A/en not_active Expired - Lifetime
- 1989-04-14 DE DE8989200938T patent/DE68902766T2/en not_active Revoked
- 1989-04-14 AT AT89200938T patent/ATE80407T1/en not_active IP Right Cessation
- 1989-04-14 EP EP89200938A patent/EP0339712B1/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1669114A1 (en) * | 1965-09-02 | 1971-12-23 | Dow Chemical Co | Thickener for aqueous latex coatings |
EP0127950A1 (en) * | 1983-05-03 | 1984-12-12 | Rheox International, Inc. | Preparation of water dispersible, modified polyurethanes |
EP0250943A2 (en) * | 1986-06-12 | 1988-01-07 | DeSoto, Inc. | Nonionic associative thickeners |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0566911A1 (en) * | 1992-04-20 | 1993-10-27 | Aqualon Company | Improved leveling aqueous coating compositions |
WO1997025382A1 (en) * | 1996-01-09 | 1997-07-17 | Henkel Kommanditgesellschaft Auf Aktien | Liquid preparation of thickening agents (ii) |
EP1464317A1 (en) * | 1998-02-13 | 2004-10-06 | L'oreal | Cosmetic composition based on associative polyurethanes and non-ionic polymers with fatty chains |
WO1999040893A1 (en) * | 1998-02-13 | 1999-08-19 | L'oreal | Cosmetic composition based on associative polyurethane and non-ionic polymers with fatty chains |
FR2774899A1 (en) * | 1998-02-13 | 1999-08-20 | Oreal | COSMETIC COMPOSITION BASED ON ASSOCIATIVE POLYURETHANS AND NON-IONIC FATTY CHAIN POLYMERS |
US6258367B1 (en) | 1998-02-13 | 2001-07-10 | L'oreal | Cosmetic composition comprising at least one nonionic amphiphilic associative polyurethane and at least one quaternary silicone |
US6572869B2 (en) | 1998-02-13 | 2003-06-03 | L'oreal S.A. | Cosmetic compositions comprising at least one catonic polymer and at least one nonionic associative polymer |
US6613315B1 (en) | 1998-02-13 | 2003-09-02 | L'oreal S.A. | Cosmetic composition comprising at least one nonionic amphiphilic associative polyurethane and at least one nonionic polymer with fatty chains |
EP0979850A1 (en) * | 1998-08-11 | 2000-02-16 | Hercules Incorporated | Use of aqueous protective coating compositions for industrial coatings and aqueous coating compositions |
EP1464686A1 (en) * | 2003-04-02 | 2004-10-06 | Reinol S.p.A. | Pseudoplastic water based ink for ball-point pen |
US6926765B2 (en) | 2003-04-02 | 2005-08-09 | Reinol S.P.A. | Pseudoplastic water based ink for ball point pen |
CN100344712C (en) * | 2003-04-02 | 2007-10-24 | 雷诺尔有限公司 | Water based ink for ball-point pen |
WO2008125977A2 (en) * | 2007-04-17 | 2008-10-23 | Akzo Nobel Coatings International B.V. | A painting apparatus |
WO2008125977A3 (en) * | 2007-04-17 | 2009-04-09 | Akzo Nobel Coatings Int Bv | A painting apparatus |
GB2461439A (en) * | 2007-04-17 | 2010-01-06 | Akzo Nobel Coatings Int Bv | A painting apparatus |
US8596898B2 (en) | 2007-04-17 | 2013-12-03 | Akzo Nobel Coatings International B.V. | Paint roller assembly |
US8632271B2 (en) | 2007-04-17 | 2014-01-21 | Akzo Nobel Coatings International B.V. | Painting apparatus |
US8790033B2 (en) | 2007-04-17 | 2014-07-29 | Akzo Nobel Coatings International B.V. | Painting apparatus |
Also Published As
Publication number | Publication date |
---|---|
EP0339712B1 (en) | 1992-09-09 |
ATE80407T1 (en) | 1992-09-15 |
SE8801594D0 (en) | 1988-04-28 |
SE459096B (en) | 1989-06-05 |
US5002985A (en) | 1991-03-26 |
DE68902766D1 (en) | 1992-10-15 |
DE68902766T2 (en) | 1993-02-04 |
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